4.alpha.,6-Dihydroxy-5-iodo-2.beta .-aryloxymethyl-3.alpha.-tetrahydropyranoacetic acid .gamma.-lactone, 6-alkyl ethers
The present specification provides novel intermediates and novel processes for the synthesis of Thromboxane B.sub.2 (11a-homo-11a-oxa-PGF.sub.2.sub..alpha.), its 15-epimer, and various carboxyl derivatives thereof. In particular, there are disclosed various bicyclic tetrahydropyran-containing lactones useful in the above processes, and corresponding acyclic lactones.
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The present invention relates to thromboxane B.sub.2 and associated intermediates and processes for which the essential material constituting a disclosure therefor is incorporated by reference here from Ser. No. 676,890, filed Apr. 14, 1976, now pending issuance as a United States Patent.
Claims
1. A thromboxane intermediate of the formula ##STR1## wherein R.sub.34 is an arylmethyl hydroxy-hydrogen replacing group selected from the group consisting of
- (a) benzyl,
- (b) benzyl substituted by one to five alkyl of one to four carbon atoms, inclusive, chloro, bromo, iodo, fluoro, nitro, phenylalkyl of 7 to 12 carbon atoms, inclusive,
- (c) benzhydryl,
- (d) benzhydryl substituted by one to ten alkyl of one to four carbon atoms, inclusive, chloro, bromo, iodo, fluoro, nitro, phenylalkyl to 7 to 12 carbon atoms, inclusive,
- (e) trityl, and
- (f) trityl substituted by one to 15 alkyl of one to four carbon atoms, inclusive, chloro, bromo, iodo, fluoro, nitro, phenylalkyl of 7 to 12 carbon atoms, inclusive;
- And wherein R.sub.33 is alkyl of one to 5 carbon atoms, inclusive.
2. 6.alpha.- OR 6.beta.-METHOXY-5.beta.-IODO-4.alpha.-HYDROXY-2.beta.-BENZYLOXYMETHYL-3.al pha.-TETRAHYDROFURAN ACETIC ACID,.gamma.-LACTONE, A THROMBOXANE INTERMEDIATE ACCORDING TO CLAIM 1.
3806540 | April 1974 | Martel |
Type: Grant
Filed: Apr 14, 1976
Date of Patent: Jun 28, 1977
Assignee: The Upjohn Company (Kalamazoo, MI)
Inventor: Robert C. Kelly (Kalamazoo, MI)
Primary Examiner: Cecilia M. Jaisle
Attorney: Robert A. Armitage
Application Number: 5/676,895
International Classification: C07D49304;